Succinic anhydride → HCID 68560648, compound

HRID 383989Notes

Reaction equation

HRID 383989 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][NH:22][CH:23]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1>CC#N>[CH3:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][N:22]([C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:23]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 24257440HCID 24257440, compound

Product 1

HCID 68560648HCID 68560648, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

25.5 g (255 mmol) of succinic anhydride and 20.3 ml (146 mmol) of NEt3 were added in succession to a solution of 16.3 g of the crude product 7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline from a) in MeCN (300 ml) and the mixture was stirred for 16 h at RT. It was then concentrated to small volume under vacuum. The residue was taken up with DCM (400 ml). It was then washed with a saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM (2×400 ml). The collected organic phases were washed with 1N aqueous hydrochloric acid (400 ml) and with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (gradient heptane/EE 1:1 heptane/EE/AcOH 2:2:1) of the residue and subsequent crystallisation of the residue from EE produced 6.79 g (21 mmol, 24% over 2 stages) of 4-(7-methyl-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-oxobutyric acid.

Workup

  1. concentrationIt was then concentrated to small volume under vacuum
  2. washIt was then washed with a saturated aqueous NaHCO3 solution
  3. extractionThe aqueous phase was extracted with DCM (2×400 ml)
  4. washThe collected organic phases were washed with 1N aqueous hydrochloric acid (400 ml) and with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customColumn chromatography (gradient heptane/EE 1:1 heptane/EE/AcOH 2:2:1) of the residue and subsequent crystallisation of the residue from EE

Sources & evidence

ORD record
ord-311da410371946c3b519371bee67337c
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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